Glibornuride
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Preferred IUPAC name
N-{[(1S,2S,3R,4R)-3-Hydroxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl]carbamoyl}-4-methylbenzene-1-sulfonamide | |
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3D model (JSmol)
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DrugBank | |
ECHA InfoCard | 100.043.735 ![]() |
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KEGG | |
MeSH | C073323 |
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Properties | |
Chemical formula
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C18H26N2O4S |
Molar mass | 366.48 g/mol |
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ATC code
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A10BB04 (WHO) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Infobox references | |
Glibornuride (INN) is an anti-diabetic drug from the group of sulfonylureas.[1] It is manufactured by MEDA Pharma and sold in Switzerland under the brand name Glutril.[2]
Synthesis[]
![](http://upload.wikimedia.org/wikipedia/commons/thumb/1/1d/Glibornuride_synthesis.svg/700px-Glibornuride_synthesis.svg.png)
Glibornuride synthesis:[3] See also: U.S. Patent 3,770,761; eidem, U.S. Patent 3,654,357 (to Hoffmann-La Roche).
Gliburnide is an endo-endo derivative made from camphor-3-carboxamide by borohydride reduction (exo approach), followed by Hofmann rearrangement to carbamate, followed by displacement with sodium tosylamide.
References[]
- ^ Haupt E, Köberich W, Beyer J, Schöffling K (December 1971). "Pharmacodynamic aspects of tolbutamide, glibenclamide, glibornuride and glisoxepide. I. Dose response relations and repeated administration in diabetic subjects". Diabetologia. 7 (6): 449–54. doi:10.1007/bf01212061. PMID 5004178.
- ^ "Glutril — Drugs.com". Drugs.com. Retrieved 12 July 2016.
- ^ Bretschneider, H.; Hohenlohe-Oehringen, K.; Graßmayr, K. (1969). "Arylsulfonylureido- und Arylsulfonylamidoacyl-derivate von Oxy- und Oxo-cycloalkanen als potentielle Antidiabetica". Monatshefte für Chemie. 100 (6): 2133. doi:10.1007/BF01151769.
Categories:
- Potassium channel blockers
- Secondary alcohols
- 1-(Benzenesulfonyl)-3-cyclohexylureas
- P-Tosyl compounds
- Gastrointestinal system drug stubs